Wang Xizhi, is traditionally referred to as the Sage of Calligraphy, and his most famous work is Lanting Xu (Preface to the Poems Composed at the Orchid Pavilion). Lanting Xu is highly appreciated not only for the aesthetic form of the manuscript, but also its philosophical expressions, which are considered important materials for analyzing Wang Xizhi’s views on life and death. He was forced to struggle for the social position of the Wang family as its patriarch, although he used to yearn for a secluded life. This article focuses on the texts of Lanting Xu and some related short letters, to delineate Wang Xizhi’s original philosophy of life, typified by the idea “obtaining pleasure from the present”.